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Literature summary for 1.3.1.9 extracted from

  • Sink, R.; Sosic, I.; Zivec, M.; Fernandez-Menendez, R.; Turk, S.; Pajk, S.; Alvarez-Gomez, D.; Lopez-Roman, E.M.; Gonzales-Cortez, C.; Rullas-Triconado, J.; Angulo-Barturen, I.; Barros, D.; Ballell-Pages, L.; Young, R.J.; Encinas, L.; Gobec, S.
    Design, synthesis, and evaluation of new thiadiazole-based direct inhibitors of enoyl acyl carrier protein reductase (InhA) for the treatment of tuberculosis (2015), J. Med. Chem., 58, 613-624.
    View publication on PubMed
Search for more literature for 1.3.1.9

Inhibitors

Inhibitors Comment Organism Structure
1-(4-methyl-1,3-thiazol-2-yl)-1-(5-[[6-(morpholin-4-yl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-(4-methyl-1,3-thiazol-2-yl)-1-(5-[[6-(piperidin-1-yl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-(4-methyl-1,3-thiazol-2-yl)-1-(5-[[6-(trifluoromethyl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-(4-methyl-1,3-thiazol-2-yl)-1-[5-[(1-methyl-1H-1,2,3-triazol-4-yl)amino]-1,3,4-thiadiazol-2-yl]ethan-1-ol
-
 Mycobacterium tuberculosis
1-(4-methyl-1,3-thiazol-2-yl)-1-[5-[(pyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]ethan-1-ol
-
 Mycobacterium tuberculosis
1-(4-methyl-1,3-thiazol-2-yl)-1-[5-[(pyrimidin-2-yl)amino]-1,3,4-thiadiazol-2-yl]ethan-1-ol
-
 Mycobacterium tuberculosis
1-(5-[[5-bromo-6-(trifluoromethyl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-(3-bromo-4-fluoroanilino)-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(1-methyl-1H-pyrazol-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(1-methyl-1H-pyrazol-4-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(2-methoxypyridin-4-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(2-methylpyridin-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(5-bromo-6-methylpyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(5-bromopyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(5-fluoropyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(5-methylpyridin-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(6-bromopyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(6-cyclopropylpyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(6-fluoropyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(6-methoxypyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(6-methylpyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
1-[5-[(6-methylpyridin-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
-
 Mycobacterium tuberculosis
4-methylthiazole
-
 Mycobacterium tuberculosis
6-([5-[1-hydroxy-1-(4-methyl-1,3-thiazol-2-yl)ethyl]-1,3,4-thiadiazol-2-yl]amino)pyridin-2-ol
-
 Mycobacterium tuberculosis
isoniazid
-
 Mycobacterium tuberculosis
triclosan
-
 Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
an acyl-[acyl-carrier protein] + NAD+ Mycobacterium tuberculosis
-
 a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 r
an acyl-[acyl-carrier protein] + NAD+ Mycobacterium tuberculosis H37Rv
-
 a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 r

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis
-
-
-
Mycobacterium tuberculosis H37Rv
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-trans-dodecenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis dodecanoyl-CoA + NAD+
-
 ?
2-trans-dodecenoyl-CoA + NADH + H+
-
 Mycobacterium tuberculosis H37Rv dodecanoyl-CoA + NAD+
-
 ?
an acyl-[acyl-carrier protein] + NAD+
-
 Mycobacterium tuberculosis a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 r
an acyl-[acyl-carrier protein] + NAD+
-
 Mycobacterium tuberculosis H37Rv a trans-2,3-dehydroacyl-[acyl-carrier protein] + NADH + H+
-
 r

Synonyms

Synonyms Comment Organism
enoyl acyl carrier protein reductase
-
 Mycobacterium tuberculosis
InhA
-
 Mycobacterium tuberculosis

Cofactor

Cofactor Comment Organism Structure
NAD+
-
 Mycobacterium tuberculosis
NADH
-
 Mycobacterium tuberculosis

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.000013
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(6-bromopyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000018
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(4-methyl-1,3-thiazol-2-yl)-1-(5-[[6-(trifluoromethyl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)ethan-1-ol
0.000046
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(5-[[5-bromo-6-(trifluoromethyl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000077
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(6-cyclopropylpyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000179
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(5-bromo-6-methylpyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000197
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(5-bromopyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.00026
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(6-methylpyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000264
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(6-methoxypyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000299
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(4-methyl-1,3-thiazol-2-yl)-1-(5-[[6-(piperidin-1-yl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)ethan-1-ol
0.000363
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(5-fluoropyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000386
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(4-methyl-1,3-thiazol-2-yl)-1-[5-[(pyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]ethan-1-ol
0.000551
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(6-fluoropyridin-2-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000741
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(2-methoxypyridin-4-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.000894
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(1-methyl-1H-pyrazol-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(4-methyl-1,3-thiazol-2-yl)-1-(5-[[6-(morpholin-4-yl)pyridin-2-yl]amino]-1,3,4-thiadiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 6-([5-[1-hydroxy-1-(4-methyl-1,3-thiazol-2-yl)ethyl]-1,3,4-thiadiazol-2-yl]amino)pyridin-2-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(4-methyl-1,3-thiazol-2-yl)-1-[5-[(pyrimidin-2-yl)amino]-1,3,4-thiadiazol-2-yl]ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(5-methylpyridin-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(6-methylpyridin-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(2-methylpyridin-3-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-(3-bromo-4-fluoroanilino)-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-[5-[(1-methyl-1H-pyrazol-4-yl)amino]-1,3,4-thiadiazol-2-yl]-1-(4-methyl-1,3-thiazol-2-yl)ethan-1-ol
0.001
-
 IC 50 above 0.001 mM, at 37°C, pH not specified in the publication Mycobacterium tuberculosis 1-(4-methyl-1,3-thiazol-2-yl)-1-[5-[(1-methyl-1H-1,2,3-triazol-4-yl)amino]-1,3,4-thiadiazol-2-yl]ethan-1-ol
0.004
-
 at 37°C, pH not specified in the publication Mycobacterium tuberculosis 4-methylthiazole